Preparation of defined molecular species of lactosylceramide by chemical deacylation and reacylation with N-succinimidyl fatty acid esters.

Abstract:

:A procedure for the preparation of specific molecular species of D-erythro-lactosylceramide involving deacylation and reacylation of lactosylceramide prepared from bovine brain gangliosides is described. Lactosylceramide was N-deacylated by alkaline hydrolysis and the resulting four lysolactosylceramides, which contained d18:1, d20:1, d18:0 and d20:0 long-chain bases, were simultaneously re-N-acylated with the N-succinimidyl ester of either 16:0, 18:0, 20:0, 22:0, 24:0, 20:1, 22:1 or 24:1 fatty acid. The resulting lactosylceramide contained four molecular species of lactosylceramides, i.e., d18:1, d20:1, d18:0 and d20:0 long-chain bases coupled with the fatty acid that was introduced. Lactosylceramides prepared in this manner were separated into four individual molecular species by high-performance liquid chromatography (HPLC). Each of the purified molecular species of lactosylceramide was quantitated by HPLC after derivatization with benzoylchloride and was characterized by mass spectrometry. The yields of reacylated lactosylceramide were 38-58% relative to the starting lactosylceramide; the purity of each of the molecular species of lactosylceramide was greater than 95%.

journal_name

Lipids

journal_title

Lipids

authors

Kadowaki H,Grant MA

doi

10.1007/BF02538917

subject

Has Abstract

pub_date

1994-10-01 00:00:00

pages

721-5

issue

10

eissn

0024-4201

issn

1558-9307

journal_volume

29

pub_type

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